Isobutylboronic Acid

Base Information

• Chemical Name: Isobutylboronic Acid
• CAS No.: 84110-40-7
• Molecular Formula: C4H11BO2
• Molecular Weight: 101.941
• Hs Code.: 29319090
• UNII: KHX76H7JHZ
• DSSTox Substance ID: DTXSID70370282
• Nikkaji Number: J914.587G
• Wikidata: Q72484985
• Mol file: 84110-40-7.mol

Synonyms:Isobutylboronic Acid;84110-40-7;Isobutaneboronic acid;2-Methylpropylboronic acid;(2-Methylpropyl)boronic acid;1-Isobutaneboronic Acid;isobutylboric acid;Boronic acid, (2-methylpropyl)-;Boronic acid, B-(2-methylpropyl)-;MFCD00134156;KHX76H7JHZ;2-Methylpropane boronic acid;B-(2-Methylpropyl)boronic acid;(2-Methylpropyl)boronicacid;IsobutylboronicAcid;Isobutyl boronic acid;2-Methylpropylboroic acid;i-BuB(OH)2;UNII-KHX76H7JHZ;2-methylpropaneboronic acid;2-methylpropyl boronic acid;2-methyl propyl boroic acid;SCHEMBL125840;2-Methyl-1-propylboronic acid;DTXSID70370282;ZAZPDOYUCVFPOI-UHFFFAOYSA-N;BCP12813;AKOS000264708;AB03722;AM80872;AS-3103;CS-W000978;AC-24794;SY002441;(2-Methylpropyl)boronic acid, >=95.0%;FT-0648068;I0597;EN300-74361;Q-101087;F0001-2138;Z1098324138

Chemical Property of Isobutylboronic Acid

Chemical Property:

• Appearance/Colour: white flake
• Vapor Pressure: 0.27mmHg at 25°C
• Melting Point: 108-111 °C
• Refractive Index: 1.398
• Boiling Point: 180 °C at 760 mmHg
• PKA: 10.49±0.43(Predicted)
• Flash Point: 62.7 °C
• PSA: 40.46000
• Density: 0.91 g/cm³
• LogP: 0.11520
• Storage Temp.: 0-6°C
• Solubility.: Acetonitrile (Slightly), DMSO, Methanol (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 102.0852098
• Heavy Atom Count: 7
• Complexity: 45

Purity/Quality:

98% ^*data from raw suppliers

Isobutylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(CC(C)C)(O)O
• Description: Isobutaneboronic acid is also known as isobutylboronic acid. Isobutaneboronic acid has been used to synthesize potent and selective dipeptidyl boronic acid proteasome inhibitors, which are promising therapeutics to treat cancer and inflammatory diseases.1
• Uses: suzuki reaction 2-Methylpropylboronic Acid is used in the preparation of isocoumarin analogs as inhibitors of γ-secretase cleavage. Also used in the preparation of peptide boronc acid. (2-Methylpropyl)boronic acid can be used as:A reactant in the preparation of 4-isobutylisoquinoline from 4-bromoisoquinoline by Suzuki-Miyaura type couple reaction.A catalyst along with aluminum hydroxide, boric acid in the polymerization of styrene.It can also be used as a reactant in:Copper catalyzed cross-coupling reactions.The synthesis of polyborylalkanes by Ir-catalyzed C-H borylation reaction.The preparation of heterosubstituted diazaboroles and borinines.

Technology Process of Isobutylboronic Acid

There total 12 articles about Isobutylboronic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

trifluoro(isobutyl)- λ4-borane potassium salt → Dihydroxy-isobutyl-boran (84110-40-7)

Guidance literature:

With water; silica gel; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo901441u

Reference yield: 62.8%

→ Dihydroxy-isobutyl-boran (84110-40-7) + 2-isobutyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (67562-20-3)

Guidance literature:

Reference yield:

Me2(CH2)2NHOB-C4H9-iso (112980-86-6) → 4-amino-4-methylpentan-2-ol (4404-98-2) + 2,4,4,6-tetramethyl-5,6-dihydro-4H-1,3-oxazine (26939-18-4) + Dihydroxy-isobutyl-boran (84110-40-7)

Guidance literature:

With sulfuric acid; acetonitrile; In n-heptane; at 0 ℃; for 5h; Title compound not separated from byproducts;

upstream raw materials:

triisobutylborane

isobutyl-bis-isobutylperoxy-borane

isobutylboric acid dibutyl ester

Me₂(CH₂)2NHOB-C₄H₉-iso

Downstream raw materials:

2-methyl-propan-1-ol

phenylarsonic acid

2-isobutyl-4-methyl-1,3,2-dioxaborinane

2-(2-methylpropyl)-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole

Refernces

• 1、 Molander, Gary A.,Cavalcanti, Livia N.,Canturk, Belgin,Pan, Po-Shen,Kennedy, Lauren E.. "Efficient hydrolysis of organotrifluoroborates via silica gel and water". supporting information; experimental part. p. 7364 - 7369. Retrieved 2010/01/16.
• 2、 Kuznetsov. "Reaction of 2-Isobutyl-4,4,6-Trimethyl-1,3,2-Oxazaborinane with Acetonitrile". . p. 127 - 128. Retrieved 2007/10/03.